A method for producing an aldehyde by reacting an olefinic compound with carbon monoxide and hydrogen in the presence of a group 8 to 10 metal compound or a group 8 to 10 metal compound and a phosphorus compound is called “hydroformylation reaction” or “oxo reaction”, and it is well-known that this method is industrially extremely valuable as a method for producing an aldehyde.
In general, in such a hydroformylation reaction, a rhodium compound or a combination of a rhodium compound and a phosphorus compound is industrially used as a catalyst. As such a phosphorus compound, for example, phosphines such as tributylphosphine, trioctylphosphine, tricyclohexylphosphine, triphenylphosphine, tri(p-tolyl)phosphine, etc. (see, for example, Patent Document 1); monophosphites such as triphenylphosphite, tri-n-butylphosphite, tris(2-t-butyl-4-methylphenyl)phosphite, etc. (see, for example, Non-Patent Documents 1 and 2); bisphosphites such as bis[3,3′,5,5′-tetra-t-butyl(1,1′-biphenyl)-2,2′-diyl]-1,2-ethyldiphosphite, bis[3,3′,5,5′-tetra-t-butyl(1,1′-biphenyl)-2,2′-diyl]-2,7,9,9-tetramethyl-9H-xanthin-4,5-diyldiphosphite, bis[3,3′-di-t-butyl-5,5′-dimethoxy(1,1′-biphenyl)-2,2′-diyl]-2,7,9,9-tetramethyl-9H-xanthin-4,5-diyldiphosphite, compounds represented by the formulae:
etc. (see, for example, Non-Patent Documents 3 and 4 and Patent Documents 2 and 3); and the like have hitherto been known, and hydroformylation reactions using such a compound have been developed.
Patent Document 1: JP-A-8-10624
Patent Document 2: JP-A-4-290551
Patent Document 3: JP-A-62-116535
Non-Patent Document 1: The Journal of Organic Chemistry, 1969, Vol. 34, No. 2, pages 327 to 330
Non-Patent Document 2: Journal of the Chemical Society, Chemical Communications, 1991, pages 1096 to 1097
Non-Patent Document 3: Organometallics, 1996, Vol. 15, pages 835 to 847
Non-Patent Document 4: Helvetica Chimica Acta, 2001, Vol. 84, pages 3269 to 3280